7 Best Weekend Getaways From Chesapeake, VA

You deserve a break from your daily routine — enjoy a relaxing getaway in Chesapeake, Virginia and the surrounding area. From beaches to mountain retreats, there are many unforgettable attractions and activities within easy driving distance of your Chesapeake vacation rental. To get you started on your itinerary, here’s a list of the seven top weekend getaways from this historic city.

1. Raleigh, North Carolina

As North Carolina’s capital city, Raleigh has a lot to offer over a short weekend trip. In three hours, you arrive in the town that’s part of the Research Triangle area and home to a couple of top-notch universities. Take a tour of the Videri Chocolate Factory and enjoy a snack after seeing how they make their delicious treats. Afterward, cross the street for dinner at The Pit, home to some of the best Carolina barbecue in the state. See the assembled animal skeletons and try the interactive exhibits at the North Carolina Museum of Natural Sciences. The Marbles Kids Museum is a favorite among children who make Tree Music and catch an educational film at the IMAX theater.

2. Calabash, North Carolina

Known locally as the Seafood Capital, Calabash, North Carolina is well worth the drive of almost five hours. This sleepy little coastal town is known for its Calabash-style of deep fat frying seafood of all kinds, so stop in at any of the locally owned restaurants, such as Captain Nance’s Seafood, for a meal. Book a day with Hurricane Fleet Charter Fishing to find all the best fishing holes and come back with a cooler full of fish. Spend a day on Bird Island, where the beaches are pristine and the surf beckons your kids to cool off. It’s also home to the Kindred Spirit mailbox. Share your experience on the island in the journal and return it to the mailbox for the next person to read.

3. Roanoke, Virginia

Unwind and relax in the quiet little town of Roanoke, Virginia. This town sits a little over four and a half hours from your home. Spend an afternoon in the Mill Mountain Park and check out the Roanoke Star as you hike or enjoy a picnic lunch. When the sun sets, look back towards the mountain and see the star, a large neon sign, lighting the sky. The Virginia Museum of Transportation has a tremendous number of antique cars, trains, and planes for you to see as you wander through the massive space. Explore the Mill Mountain Zoo with its quaint selections of exotic and native animals and hop on the train for a ride around the park.

4. Lewes, Delaware

In only three hours, put your home in the rearview mirror and arrive at your vacation rental in Lewes, Delaware. Cape Henlopen State Park has beautiful beaches for a day spent working on your tan or trying your hand at surfing. If the weather is a little cool, hike around the park and explore the remains of the military installation in the park. Climb to the top of the observation tower to see for miles around. Learn more about the local history and the Dutch who were part of the original settlers at the Zwaanendael Museum. See the sunset from a boat when you book an evening cruise from Cape Water Tours.

5. Winston-Salem, North Carolina

Nestled in the Blue Ridge Mountains, Winston-Salem, North Carolina, provides fresh air and outdoor activities for your family. Driving time is a little over four hours to your weekend retreat. Stretch your legs and enjoy the hiking trails in the Historic Bethabara Park. Once home to the religious village of the Moravians, the park is a refuge for more than 160 bird species – don’t forget your binoculars and field guide. Triad ECO Adventures leads visitors through the downtown area for tours on Segways. If you’ve never ridden before, don’t worry. They meet a few minutes early to get you upright and on the move.

6. Ocean City, Maryland

Arrive in Ocean City, Maryland, in a little less than three hours drive time for the quintessential beach trip. After a day on the beach, the Ocean City Boardwalk is the place for people watching and playings. With two locations in town, the Jolly Roger Amusement Park offers roller coasters, thrill rides, and kiddie rides. Both locations have a carnival feel, including a midway full of games and food vendors. Many shipwrecks have occurred in the area through the centuries, and the Discoversea Shipwreck Museum is the place to see some of their recovered treasures while the Ocean City Life-Saving Station teaches you about the men who risked their lives to save the sailors.

7. Dover, Delaware

Another capital city, Dover, Delaware, treats your family to a weekend of history and fun after your car trip that takes a little over three and a half hours. Find out more about farm life in the 1800s with a visit to the Delaware Agricultural Museum and Village. After learning about the state’s rich agricultural history, step over to the village that lets you experience farm life from another century. Find out more about military aviation with a tour of the Air Mobility Command Museum. Located inside a restored airport hanger, this museum houses many vintage aircraft.